Sodium Hydroxide → 4-(2-(2-Carboxy-ethyl)-3-{6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric acid

HRID 418083Notes

Reaction equation

HRID 418083 reaction equation
C([O:3][C:4](=[O:49])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24]([C:32]3[CH:41]=[CH:40][C:35]4[O:36][CH2:37][CH2:38][O:39][C:34]=4[CH:33]=3)[CH:23]=2)[C:10]=1[CH2:42][CH2:43][C:44]([O:46]CC)=[O:45])C.[OH-].[Na+]>>[C:44]([CH2:43][CH2:42][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:29])=[O:30])[CH:25]=[C:24]([C:32]3[CH:41]=[CH:40][C:35]4[O:36][CH2:37][CH2:38][O:39][C:34]=4[CH:33]=3)[CH:23]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:49])=[O:3])([OH:46])=[O:45]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 578630814-(2-(2-Ethoxycarbonyl-ethyl)-3-{6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester

Product 1

HCID 578630304-(2-(2-Carboxy-ethyl)-3-{6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric acidYield 69.7%

Procedure

A similar procedure as described in Example 40, step 8 was used, starting from 4-(2-(2-ethoxycarbonyl-ethyl)-3-{6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester (330 mg, 0.47 mmol) and 1.0 N aqueous sodium hydroxide (4.74 mL) to afford 4-(2-(2-carboxy-ethyl)-3-{6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric acid (210 mg, 69%) as a white solid: ES(+)-HRMS m/e calcd for C34H40O10S (M+Na)+ 663.2234, found 663.2229.

Sources & evidence

ORD record
ord-b92afd3bf5f84629b42ce6123c1b6fef
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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